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20 Jul - 21 Jul
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25 Jul - 27 Jul
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Top Holiday Rentals in Winter Haven

Vacation Village at Parkway
Relax by the resort's central pool, surrounded by lounge chairs and umbrellas.

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2540)
"Very nice place to stay."
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Experience a luxurious atmosphere in our spacious lobby, surrounded by palm trees, large plants, and vibrant bird murals.

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1502)
"Wonderful property and location!"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Summer Bay Orlando by Exploria Resorts
Relax by the central pool surrounded by palm trees and lounge chairs.

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5544)
"Would definitely stay again!"
The price is ₹10,081
₹14,059 total
includes taxes & fees
3 Aug - 4 Aug
Summer Bay Orlando by Exploria Resorts
Reunion Resort & Golf Club
Surrounded by lush greenery and palm trees, this resort offers multiple pools and a lazy river.

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1346)
"Great Resort."
Reunion Resort & Golf Club
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1845)
"Wonderful place to stay, staff were so nice. Would stay there every time we came to florida"
The price is ₹9,898
₹12,113 total
includes taxes & fees
27 Jul - 28 Jul
The Berkley, Orlando
Barefoot'n Resort Kissimmee Orlando
Stunning two-story home with a vibrant facade, front porch, and blue-trimmed door.

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (122)
"Great place, would definitely stay there again "
The price is ₹8,624
₹10,863 total
includes taxes & fees
30 Jul - 31 Jul
Barefoot'n Resort Kissimmee Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
Relax by the resort's curved pool, surrounded by palm trees and lounge chairs.

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2946)
"Great stay "
The price is ₹7,279
₹25,278 total
includes taxes & fees
17 Aug - 18 Aug
Regal Oaks Resort Vacation Townhomes by IDILIQ
Formosa Valley Resort by UNE Homes
Relax by the pool surrounded by a spacious deck and comfortable seating.

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (159)
"Second time we stayed in this place. Spacious, clean and convenient."
Formosa Valley Resort by UNE Homes
Lifetime of Vacations Resort
Stroll along the paved walkway surrounded by lush greenery and tropical plants, leading to a charming covered seating area.

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (141)
"Very nice Very clean"
Lifetime of Vacations Resort
Grand Lake Resort
Enjoy serene views from the pier, where benches offer a peaceful spot to sit and take in the surroundings.

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (129)
"Always a great place to stay"
Grand Lake Resort
Champions Gate condos by UNE
Relax by the resort pool surrounded by lounge chairs and umbrellas, with a view of the Mediterranean-style architecture.

Champions Gate condos by UNE

4.0 star property
9.2 out of 10, Wonderful, (19)
"It was a great place to stay"
Champions Gate condos by UNE
Encantada Resort Vacation Townhomes by IDILIQ
Relax by the serene lake and enjoy the resort's central pool surrounded by lush greenery and sun loungers.

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1358)
"Stayed here 2 years in a row & we love the location & everything about the property! Staff is friendly. Definitely coming back in the future! "
Encantada Resort Vacation Townhomes by IDILIQ
Magic Village Yards, Trademark Collection by Wyndham
Relax by the pool surrounded by comfortable lounge chairs and umbrellas.

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1143)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Barefoot Suites
Surrounded by lush greenery, this dock extends over a serene body of water, offering a tranquil escape.

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1759)
"Much better than the last stay there!"
Barefoot Suites
Summerville Vacation Homes by Columbia Management
Captiva-06 (SMV104) | Private kitchen | Fridge, microwave, oven, stovetop

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very good, (151)
"Not enough parking "
Summerville Vacation Homes by Columbia Management
Royal Laguna Villas By Magical Memories
Lobby

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Relax by the pool surrounded by palm trees and lounge chairs.

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (475)
"I like the fact that they had so many amenities"
The price is ₹9,225
₹11,639 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Encore Resort
Relax by the pool surrounded by a patio area and comfortable lounge seating.

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort
Villas At Regal Palms
Relax by the pool surrounded by lush palm trees and a beautifully maintained area.

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (564)
"Great location."
Villas At Regal Palms
Bahama Bay Resort
Children can splash and play in this vibrant water area surrounded by lush greenery and palm trees.

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2084)
"Great place to stay with your family. We will definitely be back!"
Bahama Bay Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Absolutely loved my stay at this boutique hotel! Everything feels either newly built or freshly renovated-modern, chic, and thoughtfully designed from top to bottom. The atmosphere is upscale yet welcoming, and the attention to detail is hard to miss. One of the first things I noticed was how amazing the entire hotel smells, clean, fresh, and luxurious. The amenities are top-notch. The pool area is incredibly spacious and perfect for relaxing. They also have sauna and hot tub and a nice gym. Every corner of the property is beautifully maintained. The staff was warm and professional, making my stay even more enjoyable. I’m already looking forward to coming back on my next trip to Orlando. Highly recommend!"
Ellina 1-night trip
Posted 1 day ago
Kompose Boutique Resort at Theme Parks

Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What are some of the best holiday rentals that Winter Haven has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Haven offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Haven?

Choose from 146 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Indigo's Family Fun Center, whereas The Circle B Bar Reserve and Rotary Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.